Preheat oven to 400°. Line a baking sheet with parchment and fit with a wire rack; set aside.
Halve dates lengthwise being careful not to cut all the way through. Place a small amount of cheese in the center of each date. Wrap a piece of bacon around each date making sure the ends meet underneath the date.
Place dates, seam side down, on prepared baking sheet. Bake until bacon fat is beginning to render out, about 15 minutes.
Meanwhile, in a small bowl, mix together maple syrup, red pepper flakes, rosemary, and black pepper. Brush each date with maple syrup mixture.
Continue to bake brushed dates until bacon is crispy, 15 to 20 minutes more.